(2R,4R,5R,6S)-2-Allyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester | 331475-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R,5R,6S)-2-Allyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS: 331475-75-3
• 化学式: C₃₂H₃₆O₈
• 分子量: 548.633
• InChiKey: LDDQKLHWPMSBQZ-ICDXLYTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  40.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  103.68
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2R,4R,5R,6S)-2-Allyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 在 2,6-二甲基吡啶 、 [Ir(H₂)(cod)(MePh₂P)2]PF₆ 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.83h， 生成 benzyl (7,8-di-O-benzyl-4,5-di-O-tert-butyldimethylsilyl-3-deoxy-D-manno-oct-1-ulopyrano-syl)onate fluoride
  参考文献：
  名称：

  First Total Synthesis of the Re-Type Lipopolysaccharide

  摘要：

  Three sequential efficient glycosylation reactions starting from D-glucosamine were used in the first total synthesis of Escherichia coli Re lipopolysaccharide, which is one of the most simple lipopolysaccharides found on the surface of living bacteria.

  DOI：

  10.1002/1521-3773(20010417)40:8<1475::aid-anie1475>3.0.co;2-v
• 作为产物：
  描述：

  (3aR,4R,6R,7aR)-6-Allyloxy-4-((R)-1,2-bis-benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid benzyl ester 在 溶剂黄146 作用下， 反应 1.0h， 以92%的产率得到(2R,4R,5R,6S)-2-Allyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  First Total Synthesis of the Re-Type Lipopolysaccharide

  摘要：

  Three sequential efficient glycosylation reactions starting from D-glucosamine were used in the first total synthesis of Escherichia coli Re lipopolysaccharide, which is one of the most simple lipopolysaccharides found on the surface of living bacteria.

  DOI：

  10.1002/1521-3773(20010417)40:8<1475::aid-anie1475>3.0.co;2-v

文献信息

• Stereoselective Glycosylation of 3-Deoxy-d-manno-2-octulosonic Acid with Batch and Microfluidic Methods
  作者：Yukari Fujimoto、Atsushi Shimoyama、Koichi Fukase

  DOI：10.1055/s-0030-1260313

  日期：2011.10

  A practical and efficient stereoselective synthesis of 3-deoxy-d-manno-2-octulosonic acid (Kdo) glycoside was achieved using N-trifluoroacetoimidate as the glycosyl donor with both batch and microfluidic methods. The method used a conformationally constrained glycosyl donor, which has a bulky isopropylidene group at the 4,5-O-position. The strained conformation directed the coordination of the acetonitrile

  3-脱氧的一种实用和有效的立体选择性合成d使用达到-manno -2-辛酮糖酸（KDO）糖苷Ñ -trifluoroacetoimidate与分批和微流体方法的糖基供体。该方法使用构象受限的糖基供体，其在4，5-O-位具有大的异亚丙基。应变的构象指示乙腈溶剂的配位，这导致糖基化反应的反应性和α-选择性增强。 糖基化-碳水化合物-立体选择性合成-碳正离子化-天然产物